CHM145L Organic Chemistry 1 Laboratory

4th Quarter SY 2014-2015

Melting Point and Boiling Point of Organic Compounds

Miranda, Marilyn1, Tardecilla, Ma. Bianca, C.2
Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; 2Student, CHM145L/A41, School of Chemical Engineering,
Chemistry and Biotechnology, Mapua Institute of Technology
1

ABSTRACT
The properties of organic compounds encompass both chemical and physical properties. Furthermore, the chemical structures
of a compound affect the different properties of a compound. The experiment showed how melting and boiling points affect the
various Organic compounds. One of the characteristics on determining the significance of the temperature values is the
intermolecular force or attractive forces between individual molecules. Sealed capillary tubes were used on both melting and
boiling point determination through heating the red end of the tube through the Bunsen burner. Melting point of compounds is
identified in order to characterize the purity of the compound and to determine an unknown compound. A Thomas Hoover
Apparatus is used in determining the melting point of the organic compounds. Each sealed capillary tube was filled with 7
different organic compounds: Benzoic acid, Benzoin, Naphthalene, Salicylic acid, Urea, Maleic acid, and Fumaric acid and
analyzed through the prepared melting point set-up. In the experiment, the Fumaric acid has the greatest melting point and the
Naphthalene. Furthermore, impurities hands out a large amount of range of melting point which means the compound,
specifically, Impure Urea, is already contaminated by nature. Moreover, the boiling point is responsible for characterizes a
certain compound and compare it with the inorganic compounds. Unlike the melting point, it is not usually used to determine
the purity of the compound since its procedure is more complicated than the Melting Point process. The micro method was
used showed that the propanoic acid alcohol showed the highest boiling point of the given compounds followed by n-butyl and
n-Butanol, sec-butyl, tert-butyl, 2-Butanone, n-Hexane, and n-Pentane. It was done through filling a just amount of glycerol on
the thiele tube and clamping it to the iron stand and placing it right above the hot plate which ranges from heat 4-5. Inserted on
the thiele tube is the test tube with 3-5 drops of liquid compounds and an inverted capillary tube. Beside it is a thermometer
secured with a rubber tubing also clamped into iron stand. It was measured through the appearance of bubbles This
experiment shows that a compound that exhibits a hydrogen bonding has the strongest force of interaction followed by the
Dipole-Dipole interaction. Correspondingly, the London dispersion force is identified as the weakest bond of intermolecular
force.
Keywords: Physical properties, Organic Compounds, Intermolecular Forces, Hydrogen Bonding, London dispersion forces, Melting Point,
Impurities, Thomas Hoover Apparatus, Boiling point, Micro method

INTRODUCTION
Organic Compounds are composed of Carbon containing
molecules and their reactions. Its corresponding properties
are basically significant to both chemical and physical
composition of compounds. A certain matters structure is
affected both through its chemical and physical properties.
The chemical properties include the behaviour of a
substance which undergoes a chemical change or reaction.
They are responsible to the reactions of reagents including
the rates of their reaction and its extent. Moreover, the
physical properties cover the physical appearance or
observation of the substance. Among of the physical
properties include the Formula, Boiling Point, Melting Point,
Density, Refractive Index, and Solubilities of Compounds.
These properties are observed and reviewed in order to
compare and determine the nature of the compound. This

analysis is commonly used on determining

characterizing an unknown organic compound.

and

Melting, by definition, is the procedure wherein the

molecules change from solid into liquid phase. The
transition between the solid and the liquid is abrupt for small
molecules which are measured to 0.1 degrees Celsius. In
order to melt a certain compound, its energy are supplied in
order to break the intermolecular forces that bind organic
molecules in its solid state to be able to go to the liquid
state. Moreover, the temperature wherein the solid and
liquid forms a pure substance can exist in equilibrium is
classified as Melting Point. Various compounds varies
melting point and could be determined by using
approximately 1 mg of the sample. Melting point is one of

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its characteristic as a physical property to pure solid organic

compounds. The force accountable for the breakage of
atoms is called the Intermolecular force. Its chemical
structures produce a wide range of intermolecular force of
attraction. Given the intermolecular force, it would be
convenient and less difficult to estimate its melting point.
The melting points of a substance increase along with the
strength of the intermolecular force. These forces are
significant in terms of how atoms interact, attract, and form
compounds. Depending on the phase of the substance, the
nature of chemical bonds, and the types of elements
present, more than one type of interaction may occur to the
total attraction of molecules. The weakest type of
intermolecular force is the London Dispersion Forces
wherein there are only temporary dipole attractions on
nonpolar molecules to one another. These attractive forces
causes nonpolar substances to condense to liquids and to
freeze into solids thus, this type of force requires low
temperature resulting to having the lowest melting point of
all types of forces. The less strong type is the Dipole-Dipole
Forces, wherein the polar compounds are attracted to one
another. The larger the dipole moment the greater force are
shown. Lastly, the strongest type of intermolecular force is
the Hydrogen Bonding it involves compounds such as O-H,
N-H, or F-H bonds. This is considered as a special type of
dipole-dipole interaction between the hydrogen atoms in a
polar bond and an electronegative O, N, or F atoms.
Moreover, it has the highest melting point. In general, the
melting point range is directly proportional to the melting
point of a substance. Correspondingly, the melting point of
a pure substance has a smaller range than an impure one.
It is basically based on the purity of the compound wherein
an impure compound will melt over a wide range of
temperatures. The experiment involves relating the melting
points of organic substances to the intermolecular forces of
attractions in these molecules.
If a liquid is heated and in time reaches a temperature
wherein the vapour pressure are enough to form bubbles in
the body of the liquid has a temperature labelled as boiling
point. This type of measurement of a temperature of a pure
organic liquid is one of its characteristic physical properties
just like the melting point. It is the temperature at which the
vapour pressure of a liquid is equal to the external
pressure. The boiling point of a liquid depends on the
surrounding environmental pressure. A normal range of
boiling point of water is at 100 degrees Celsius. In addition,
normal boiling point of a liquid is the boiling point when the
external pressure at 1 atm. Similar to melting point, the
boiling points of substances often reflects the strength of
the intermolecular forces operating among the molecules.

Sufficient energy is needed in order to trounce the attractive

forces among molecules before they can enter the vapour
phase. The highest boiling point corresponds to the
strongest intermolecular force, Hydrogen bonding, while the
lowest boiling point corresponds to the weakest
intermolecular force. Boiling points are used in order
identifying an unknown organic substance. It is more
complex than determination of melting points which
requires
more
material.
The experiment involves the two physical properties:
Melting Point and Boiling Point of Organic Compounds. The
purpose of this investigation was to determine the effect of
intermolecular forces of attraction and geometric isomerism
on the melting point of compounds and the branching on
the boiling point of organic compounds; and purity on the
melting point range of organic compounds. The two
properties were determined and compared to the other
compounds. Its relations are being understand through the
properties between compounds is the fundamental step for
the development in areas of chemistry.
MATERIALS AND METHODS
The experiment was divided into two parts. The first part
involves the melting point of solids, while, the second part
of the experiment comprises the boiling point of liquids. The
apparatus involves Thomas-Hoover Melting Point
Apparatus, Thiele tube, Hot plate, Thermometer, Micro test
tubes, and Capillary tubes. There are a total of seven test
compounds used in determination of melting points namely:
finely grounded naphthalene, benzoic acid, salicylic acid,
benzoin, fumaric acid, and pure and impure urea.
Meanwhile, for the boiling points, there were a total of eight
test compounds used in determining th boiling points of the
liquids: n-Butanol, 2-Butanone, n-Hexane, n-Pentane,
Propanoic acid, n-butyl alcohol, sec-butyl, and tert-butyl
alcohol. During the experiment, n-Butyl alcohol is the same
as the butanol and n-Pentane is replaced with n-Heptane.
The Glycerol was used for the oil bath on the determination
of the boiling point range. The experiment ran for about 4
hours.
The experiment involved the usage of capillary tubes. The
first part of the experiment was done through sealing the
end (with red mark) of the capillary tube through Bunsen
burner as seen on figure 1. This is prepared in order to
obtain both liquid and solid samples for melting and boiling

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point experiment. The sealed tube should be straight for the

melting part.

Figure 1. Sealed Capillary tube

A small amount of the solid sample was scooped through
the capillary tube with the help of the glass tubing. The tube
helps the sample to sink inside the tube until at about 1cm
length of the tube was filled. The first part of the experiment
involved using the Thomas Hoover Apparatus wherein it
determines the temperature of the sample placed in the
capillary tube as shown in figure 2. The melting point range
of the solid sample was determined using the first
temperature (T1) where the solid start to melt and the
second temperature (T2) in which the entire solid sample
turned into liquid. It was repeated to all solid samples in
determining the melting point range.

The second part of the experiment was a bit more complex

the first part and requires more time. The thiele tube was
filled with a just amount of Glycerol, just about the arm of
the tube, and was attached on the iron clamp connected to
the iron stand and placed right above the hot plate. The
next step was to set up the capillary tube is inverted and is
placed inside the micro test tube with the liquid sample at
around three to five drops. It was made sure that the
capillary tube is immersed inside the test tube. The test
tube was secured beside the thermometer through a rubber
tube. It was then attached to the iron clamp in which the
ends of the thermometer and the test tube are immersed on
the thiele tube with glycerol. It was made sure that the
rubber tube was not soaked inside the glycerol. This set-up
is called as the Boiling point apparatus set-up as seen in
figure 3. The oil bath was heated at around 4-5 on the hot
plate. The samples were observed carefully until bubbles
came out of the capillary tube and its first temperature is
recorded. Then the oil was cooled down by placing the iron
stand away from the iron stand and reheated through the
hot plate and the sample was again observed carefully until
the liquid came out from the capillary tube which means the
second temperature of the boiling point range is already
present.
Thermometer

Test tube with

capillary tube

Capillary tube
holder

Silicone fluid

Thiele tube with

glycerol

Magnifying lens
Iron Clamp

Hot plate
Power
Thermometer

Stirrer
adjusting knob

Figure 3. Boiling point Apparatus set-up

Figure 2. Thomas Hoover Apparatus set-up.

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RESULTS AND DISCUSSIONS

The results obtained from the melting point range and
boiling point range was compared to its literature value. It
was then gathered and recorded on the data. The data
obtained from the melting point is divided into three parts.
Table 1 depicts the melting point of the solid compound
according to the structural effect of the intermolecular
forces of attraction. Meanwhile, Table 2, shows the
structural effect of geometric isomers or substituent on
melting point. Table 3, shows the effect of purity on melting
point range.
Table 1. Structural Effect of Intermolecular Forces of
Attraction

other given organic samples. In the data, naphthalene

shows that the networks of Van der Waals is the only force
that holds the molecules together. This also means that the
lowest melting point within the table represents the weakest
intermolecular bond.
Table 2. Structural Effect of Geometric Isomers or
Substituent

COMPOUND

T1(C)

T2(C)

MELTING
POINT

Maleic acid

134

138

135

Fumaric acid

242

265

287

COMPOUND

T1(C)

T2(C)

MELTING
POINT

Benzoic acid

120

125

122.46

Benzoin

130

136

132

Naphthalene

78

82

80.26

Salicylic acid

156

162

159

Fumaric acid has a higher value of melting point rather than

the maleic acid despite of its similar molecular weight. This
is due to the fact that they have different intermolecular
forces. Maleic acid is known as a cis-isomer that has
intermolecular bonding compared to the fumaric acid which
is a trans-isomer. Geometric isomerism occurs when there
is a restricted rotation in a molecule. Cis-isomer is known
as wherein the identical atoms are locked on the same side
of a bond while trans-isomer mentions that the identical
atoms are on the opposite sides of the bond.

Urea

130

135

133

Table 3. Effect of Purity on Melting Point Range

The gathered data from the experimental value is then

compared to the literature value given. It is observed that
the values from T1 to T2 are close to the literature value of
the compounds. The Salicylic acid has the highest melting
point, followed by Urea, Benzoin, Benzoic acid, and the
lowest melting point is Naphthalene. Through the data
gathered this means that Salicylic acid has the greatest
intermolecular force while the Naphthalene has the least
intermolecular force between the five compounds.
Furthermore, the experimental data obtained from Benzoic
acid and Salicylic acid illustrated slightly showed
discrepancy since the range was too far from the expected
temperature of true value.
The physical properties like the melting point are affected
by the chemical structure and the attraction of opposite
charges in two or more different molecules. Salicylic acid
has an increasing number of electrostatic bonds between
its fundamental molecules because of heat compared to

COMPOUND

T1(C)

T2(C)

MELTING
POINT

Pure Urea

130

135

133

Impure Urea

98

132

133

The experimental data placed on the pure urea is identical

to the value of urea on table 1. The data obtained has a
small range of T1 and T2 since the compound being
determined is pure. It only gave 5 degrees Celsius
selection. In contrast to the values gathered from the
impure urea, which handed out 34 degrees Celsius range.
Impure urea gave a large range of melting point which
makes the melting point lower since impurities affect the
quality and structure of the compound or material.
Impurities are substances restrained in a certain compound.

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It ruins the uncontaminated transparency of a compound,

thus resulting to unreliable figures.
On the other hand, the boiling point of the liquid compounds
by a micro method were gathered and divided into two
parts. Table 4 shows the structural effect of intermolecular
forces of attraction on the boiling point. Consequently, table
5 shows the structural effect of branching. The boiling point
experiment was a complicated since it requires more time
than the first one. Errors were encountered during the
experiment both human and equipment error. An error that
occurred on the groups experiment was the capillary tube
was not inverted, so the group had to redo the set-up again.
Table 4. Structural Effect of Intermolecular Forces of
Attraction

COMPOUND

T1(C)

T2(C)

BOILING
POINT

n-Butanol

115

119

117.4

2-Butanone

76

80

79.64

n-Pentane

35

38

36.1

Propanoic acid

138

143

141.2

n-Hexane

66

69

68

alcohol
tert-butyl
alcohol

80

84

82.2

The samples are alcohols which contain carbon atoms and

tend to have strong hydrogen bonding which results to have
a large actual boiling point. Thus, n-butyl is the strongest
intermolecular force and greater number of carbon atoms,
followed by sec-butyl and tert-butyl alcohol. Furthermore,
the data gathered from the sec-butyl alcohol showed a
large range of data ranging from 96 degrees Celsius up to
100 degrees Celsius. The supposed to be value should not
give a large range since it is a pure compound.
Figure 4 is a bar graph that summarized the literature value
of the melting point of the solid compounds and on figure 5
are the boiling point of the liquid samples of the tables.

The Propanoic acid has the highest boiling point since it is

polar and forms strong hydrogen bonding while th nHexane has the lowest boiling point since there are no
hydrogen bond present. Compounds with a larger
molecular weight tend to have a stronger intermolecular
force.
Figure 4. Summarized Literature Value for Melting Point of
Solid Compounds on Tables 1-3

Table 5. Structural Effect of Branching

COMPOUND

T1(C)

T2(C)

BOILING
POINT

n-butyl
alcohol

80

84

74

sec-butyl

96

101

98-100

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3.

Chang, R., and Goldsby, K. (2011) General

Chemistry the essential concepts, 7th Ed., New
York, NY: McGraw-Hill Companies, Inc.

4.

Clark J. (2012). Chemguide. StereoisomerismGeometric Isomerism. Retrieved from:

http://www.chemguide.co.uk/basicorg/isomeris
m/geometric.html

Figure 5. Summarized Literature Value for Boiling Point on

Liquid Samples Tables 4-5
CONCLUSIONS AND RECOMMENDATIONS
Throughout the experiment, the boiling point and melting
point are gathered through the Thomas Hoover Melting
Point set-up and Boiling Point apparatus in accordingly.
They were then compared and analyzed to its literature
value and intermolecular force. Furthermore, the effect of
intermolecular force of attraction and geometric isomerism
on the melting point of compounds. Stronger intermolecular
force indicates higher melting points. The compound of the
strongest intermolecular force is known as the hydrogen
bonding while the weakest bond is classified as the
London-Dispersion force. Likewise, the melting points could
determine if a compound is a weak or a strong bond. The
geometric isomerism is also significant to the difference of
the melting point which is dependent on the shape and the
type of bond the atoms are connected. It is also shown that
the compounds with greater number of which can form
hydrogen bonds have both high melting and boiling points.
Consequently, the molecular weight indicates how strong
the intermolecular force is. The higher the molecular weight
the greater force is present. Moreover, if there are same
molecular weights but different values of melting or boiling
points, it is classified as an isomer wherein trans-isomers
forms a stronger bond and yields to a high melting point
than a cis-isomer. Compound with more branching atoms
exhibits greater boiling point. Impurities occur when there is
a large difference on the actual value that the experimental
value. Both equipment and human error may occur on the
experiment thus the procedure must be done properly and
precautions should be known in order to properly execute
and implement the equipments. Proper eye vision should
also be conducted in order to accurately gather data from
this experiment.
REFERENCES
1.
2.

Baluyot J., and De Castro K. Organic

Chemistry Laboratory Manual for Chemistry
(Part I).
Klein, D. (2012) Organic Chemistry, 1st Ed.,
Hoboken, NJ: John Wiley & Sons Inc.

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